1,2-Dimethoxyethane → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

HRID 1514007ノート

反応式

HRID 1514007 の反応式
Br[C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH:7]([C:6]1[CH:9]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=[CH:4][C:5]=1[OH:10])=[O:8]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 728635-Bromosalicylaldehyde

生成物 1

HCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde収率 78.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

In an atmosphere of argon, 496 g (2.46 mol) of 5-bromosalicylaldehyde, 361 g (2.96 mol) of phenylboronic acid, 57 g (49.0 mmol) of tetraxis(triphenylphosphine)palladium(0), 8.6 L of DME and 784 g of sodium carbonate/3.7 L of water were charged, and subjected to heating under reflux with stirring for 17 hours. After cooling the resultant to room temperature, 3 L of toluene was added, and then an aqueous layer was removed. An organic layer was washed with water, and dried with magnesium sulfate. The solvent was distilled off under a reduced pressure. The crystals were purified by silica gel chromatography, whereby 382 g of 3-formyl-4-hydroxybiphenyl was obtained (yield: 78%).

後処理

  1. temperatureto heating
  2. temperatureunder reflux
  3. customan aqueous layer was removed
  4. washAn organic layer was washed with water
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off under a reduced pressure
  7. customThe crystals were purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2177e73fe4ce40178b81097a8b81cb95
出典データセット
uspto-grants-2012_07
特許番号
US08221907B2

反応ノート

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